Symmetrical diazo compounds containing 2-pyridinium groups and cationic or non-cationic linker, compositions comprising them, method of coloring, and device

A dyeing composition comprising, in a medium appropriate for the dyeing of keratin fibers, as direct dye at least one compound of formula (I), the addition salts with an acid and/or the solvates thereof:

• wherein:
• the radicals R2, which may be identical or different, are chosen from:
• optionally substituted C1-C16 alkyl radicals optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom, said alkyl radical being further optionally substituted by at least one group chosen from thio (—SH);
• C1-C4 thioalkyl;
• C1-C4 alkylsulphinyl and C1-C4 alkylsulphonyl groups;
• hydroxyl groups,
• C1-C4 alkoxy groups,
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups (RO—CO—) in which R is chosen from C1-C4 alkyl radicals,
• alkylcarbonyloxy radicals (RCO—O—) in which R is chosen from C1-C4 alkyl radicals, alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals,
• amino groups,
• amino groups substituted by one or two identical or different C1-C4 alkyl radicals optionally carrying at least one hydroxyl group, it being possible for the two alkyl radicals optionally to form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• alkylcarbonylamino groups (RCO—NR′—) in which the radical R is chosen from C1-C4 alkyl radicals, and the radical R′ is chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminocarbonyl groups ((R)2N—CO—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups (N(R)2—CO—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminosulphonyl groups ((R)2N—SO2—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• alkylsulphonylamino groups (RSO2—NR′—) in which R is chosen from C1-C4 alkyl radicals, and R′ is chosen from hydrogen atoms and C1-C4 alkyl radicals;
• optionally substituted aryl radicals;
• optionally substituted (C1-C4)alkylaryl radicals;
• alkylsulphinyl groups (R—SO—) in which R is chosen from C1-C4 alkyl radicals;
• alkylsulphonyl groups (R—SO2—) in which R is chosen from C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• halogen atoms;
• thio groups (HS—);
• and
• alkylthio groups (RS—) in which the radical R is chosen from optionally substituted C1-C4 alkyl radicals;
• e is an integer ranging from 0 to 4;
• when e is 2, the two radicals R2 may optionally form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic, containing 5 or 6 ring members, which is optionally substituted by at least one identical or different group chosen from hydroxyl groups, C1-C4 alkyl groups, C1-C4 alkoxy groups, C2-C4 (poly)hydroxyalkoxy groups, amino groups, amino groups substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group;
• when e is less than 4, the unsubstituted carbon atom(s) of the heterocycle carry a hydrogen atom,
• the radicals R3, which may be identical or different, are chosen from:
• optionally substituted C1-C16 alkyl radicals optionally interrupted by at least one entity chosen from heteroatoms and groups comprising at least one heteroatom,
• hydroxyl groups,
• C1-C4 alkoxy groups,
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups (RO—CO—) in which R is chosen from C1-C4 alkyl radicals,
• alkylcarbonyloxy radicals (RCO—O—) in which R is chosen from C1-C4 alkyl radicals;
• alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals;
• amino groups;
• amino groups substituted by one or two identical or different C1-C4 alkyl radicals optionally carrying at least one hydroxyl group;
• it being possible for the two alkyl radicals optionally to form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• alkylcarbonylamino groups (RCO—NR′—) in which the radical R is chosen from C1-C4 alkyl radicals, and the radical R′ is chosen from a hydrogen atom and C1-C4 alkyl radicals;
• aminocarbonyl groups ((R)2N—CO—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups (N(R)2—CO—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminosulphonyl groups ((R)2N—SO2—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radical;
• alkylsulphonylamino groups (RSO2—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• thio groups (HS—);
• alkylthio groups (RS—) in which the radical R is chosen from C1-C4 alkyl radicals;
• alkylsulphinyl groups (R—SO—) in which R is chosen from C1-C4 alkyl radicals;
• alkylsulphonyl groups (R—SO2—) in which R is chosen from C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• and
• halogen atoms;
• m′ is an integer ranging from 0 to 4;
• when m′ is greater than or equal to 2, two adjacent radicals R3 may form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic, containing 6 ring members, which is optionally substituted by at least one identical or different group chosen from:
• hydroxyl groups, C1-C4 alkyl groups, C1-C4 alkoxy groups, C2-C4 (poly)hydroxyalkoxy groups, C1-C4 alkylcarbonylamino groups, amino groups, amino groups substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group,
• when m′ is less than 4, then the unsubstituted carbon atom(s) of the aromatic ring carry a hydrogen atom;
• W1 radicals, which are identical, are chosen from:
• hydrogen atoms,
• halogen atoms chosen from bromine, chlorine and fluorine, and
• —NR5R6, OR7, —NR4—Ph—NR5R6, —NR4—Ph—OR7, —O—Ph—OR7 and —O—Ph—NR5R6 groups,
• wherein:
• R4 and R7, which may be identical or different, are chosen from hydrogen atoms, optionally substituted C1-C20 alkyl radicals, optionally substituted C1-C3 aralkyl radicals, and optionally substituted phenyl radicals;
• R5 and R6, which may be identical or different, are chosen from hydrogen atoms, optionally substituted C1-C20 alkyl radicals, optionally substituted phenyl radicals, optionally substituted C1-C3 aralkyl radicals, and alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals;
• and
• R5 and R6 may optionally form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms, chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• or
• R5 and R6 may optionally form, with the carbon atom of the aromatic ring adjacent to that to which —NR5R6 is attached, a 5- or 6-membered saturated heterocycle;
• Ph is chosen from optionally substituted phenyl radicals;
• L is a cationic or non-cationic linker;
• wherein the electroneutrality of the compound of formula (I) is ensured by at least one cosmetically acceptable anion (An).

A method of coloring keratin fibers, comprising applying to the keratin fibers a composition comprising, in a medium appropriate for the dyeing of keratin fibers, as direct dye at least one compound of formula (I), the addition salts with an acid and/or the solvates thereof:

• wherein:
• the radicals R2, which may be identical or different, are chosen from:
• optionally substituted C1-C16 alkyl radicals optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom, said alkyl radical being further optionally substituted by at least one group chosen from thio (—SH);
• C1-C4 thioalkyl;
• C1-C4 alkylsulphinyl and C1-C4 alkylsulphonyl groups;
• hydroxyl groups,
• C1-C4 alkoxy groups,
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups (RO—CO—) in which R is chosen from C1-C4 alkyl radicals,
• alkylcarbonyloxy radicals (RCO—O—) in which R is chosen from C1-C4 alkyl radicals,
• alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals,
• amino groups,
• amino groups substituted by one or two identical or different C1-C4 alkyl radicals optionally carrying at least one hydroxyl group, it being possible for the two alkyl radicals optionally to form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• alkylcarbonylamino groups (RCO—NR′—) in which the radical R is chosen from C1-C4 alkyl radicals, and the radical R′ is chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminocarbonyl groups ((R)2N—CO—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups (N(R)2—CO—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminosulphonyl groups ((R)2N—SO2—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• alkylsulphonylamino groups (RSO2—NR′—) in which R is chosen from C1-C4 alkyl radicals, and R′ is chosen from hydrogen atoms and C1-C4 alkyl radicals;
• optionally substituted aryl radicals;
• optionally substituted (C1-C4)alkylaryl radicals;
• alkylsulphinyl groups (R—SO—) in which R is chosen from C1-C4 alkyl radicals;
• alkylsulphonyl groups (R—SO2—) in which R is chosen from C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• halogen atoms;
• thio groups (HS—);
• and
• alkylthio groups (RS—) in which the radical R is chosen from optionally substituted C1-C4 alkyl radicals;
• e is an integer ranging from 0 to 4;
• when e is 2, the two radicals R2 may optionally form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic, containing 5 or 6 ring members, which is optionally substituted by at least one identical or different group chosen from hydroxyl groups, C1-C4 alkyl groups, C1-C4 alkoxy groups, C2-C4 (poly)hydroxyalkoxy groups, amino groups, amino groups substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group;
• when e is less than 4, the unsubstituted carbon atom(s) of the heterocycle carry a hydrogen atom,
• the radicals R3, which may be identical or different, are chosen from:
• optionally substituted C1-C16 alkyl radicals optionally interrupted by at least one entity chosen from heteroatoms and groups comprising at least one heteroatom,
• hydroxyl groups,
• C1-C4 alkoxy groups,
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups (RO—CO—) in which R is chosen from C1-C4 alkyl radicals,
• alkylcarbonyloxy radicals (RCO—O—) in which R is chosen from C1-C4 alkyl radicals;
• alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals;
• amino groups;
• amino groups substituted by one or two identical or different C1-C4 alkyl radicals optionally carrying at least one hydroxyl group;
• it being possible for the two alkyl radicals optionally to form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• alkylcarbonylamino groups (RCO—NR′—) in which the radical R is chosen from C1-C4 alkyl radicals, and the radical R′ is chosen from a hydrogen atom and C1-C4 alkyl radicals;
• aminocarbonyl groups ((R)2N—CO—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups (N(R)2—CO—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminosulphonyl groups ((R)2N—SO2—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radical;
• alkylsulphonylamino groups (RSO2—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• thio groups (HS—);
• alkylthio groups (RS—) in which the radical R is chosen from C1-C4 alkyl radicals;
• alkylsulphinyl groups (R—SO—) in which R is chosen from C1-C4 alkyl radicals;
• alkylsulphonyl groups (R—SO2—) in which R is chosen from C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• and
• halogen atoms;
• m′ is an integer ranging from 0 to 4;
• when m′ is greater than or equal to 2, two adjacent radicals R3 may form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic, containing 6 ring members, which is optionally substituted by at least one identical or different group chosen from:
• hydroxyl groups, C1-C4 alkyl groups, C1-C4 alkoxy groups, C2-C4 (poly)hydroxyalkoxy groups, C1-C4 alkylcarbonylamino groups, amino groups, amino groups substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group,
• when m′ is less than 4, then the unsubstituted carbon atom(s) of the aromatic ring carry a hydrogen atom;
• W1 radicals, which are identical, are chosen from:
• hydrogen atoms,
• halogen atoms chosen from bromine, chlorine and fluorine, and
• —NR5R6, OR7, —NR4—Ph—NR5R6, —NR4—Ph—OR7, —O—Ph—OR7 and —O—Ph—NR5R6 groups,
• wherein:
• R4 and R7, which may be identical or different, are chosen from hydrogen atoms, optionally substituted C1-C20 alkyl radicals, optionally substituted C1-C3 aralkyl radicals, and optionally substituted phenyl radicals;
• R5 and R6, which may be identical or different, are chosen from hydrogen atoms, optionally substituted C1-C20 alkyl radicals, optionally substituted phenyl radicals, optionally substituted C1-C3 aralkyl radicals, and alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals;
• and
• R5 and R6 may optionally form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms, chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• or
• R5 and R6 may optionally form, with the carbon atom of the aromatic ring adjacent to that to which —NR5R6 is attached, a 5- or 6-membered saturated heterocycle;
• Ph is chosen from optionally substituted phenyl radicals;
• L is a cationic or non-cationic linker;
• wherein the electroneutrality of the compound of formula (I) is ensured by at least one cosmetically acceptable anion (An);
• wherein said fibers, may be dry or wet, and the composition is left on the fibers for a period of time sufficient to give the desired coloring effect.

A multi-compartment kit, comprising

• a first compartment containing a dyeing composition comprising, in a medium appropriate for the dyeing of keratin fibers, as direct dye at least one compound of formula (I), the addition salts with an acid and/or the solvates thereof:
• wherein:
• the radicals R2, which may be identical or different, are chosen from:
• optionally substituted C1-C16 alkyl radicals optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom, said alkyl radical being further optionally substituted by at least one group chosen from thio (—SH);
• C1-C4 thioalkyl;
• C1-C4 alkylsulphinyl and C1-C4 alkylsulphonyl groups;
• hydroxyl groups,
• C1-C4 alkoxy groups,
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups (RO—CO—) in which R is chosen from C1-C4 alkyl radicals,
• alkylcarbonyloxy radicals (RCO—O—) in which R is chosen from C1-C4 alkyl radicals,
• alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals,
• amino groups,
• amino groups substituted by one or two identical or different C1-C4 alkyl radicals optionally carrying at least one hydroxyl group, it being possible for the two alkyl radicals optionally to form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• alkylcarbonylamino groups (RCO—NR′—) in which the radical R is chosen from C1-C4 alkyl radicals, and the radical R′ is chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminocarbonyl groups ((R)2N—CO—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups (N(R)2—CO—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminosulphonyl groups ((R)2N—SO2—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• alkylsulphonylamino groups (RSO2—NR′—) in which R is chosen from C1-C4 alkyl radicals, and R′ is chosen from hydrogen atoms and C1-C4 alkyl radicals;
• optionally substituted aryl radicals;
• optionally substituted (C1-C4)alkylaryl radicals;
• alkylsulphinyl groups (R—SO—) in which R is chosen from C1-C4 alkyl radicals;
• alkylsulphonyl groups (R—SO2—) in which R is chosen from C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• halogen atoms;
• thio groups (HS—);
• and
• alkylthio groups (RS—) in which the radical R is chosen from optionally substituted C1-C4 alkyl radicals;
• e is an integer ranging from 0 to 4;
• when e is 2, the two radicals R2 may optionally form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic, containing 5 or 6 ring members, which is optionally substituted by at least one identical or different group chosen from hydroxyl groups, C1-C4 alkyl groups, C1-C4 alkoxy groups, C2-C4 (poly)hydroxyalkoxy groups, amino groups, amino groups substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group;
• when e is less than 4, the unsubstituted carbon atom(s) of the heterocycle carry a hydrogen atom,
• the radicals R3, which may be identical or different, are chosen from:
• optionally substituted C1-C16 alkyl radicals optionally interrupted by at least one entity chosen from heteroatoms and groups comprising at least one heteroatom,
• hydroxyl groups,
• C1-C4 alkoxy groups,
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups (RO—CO—) in which R is chosen from C1-C4 alkyl radicals,
• alkylcarbonyloxy radicals (RCO—O—) in which R is chosen from C1-C4 alkyl radicals;
• alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals;
• amino groups;
• amino groups substituted by one or two identical or different C1-C4 alkyl radicals optionally carrying at least one hydroxyl group;
• it being possible for the two alkyl radicals optionally to form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• alkylcarbonylamino groups (RCO—NR′—) in which the radical R is chosen from C1-C4 alkyl radicals, and the radical R′ is chosen from a hydrogen atom and C1-C4 alkyl radicals;
• aminocarbonyl groups ((R)2N—CO—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups (N(R)2—CO—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• aminosulphonyl groups ((R)2N—SO2—) in which the radicals R, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radical;
• alkylsulphonylamino groups (RSO2—NR′—) in which the radicals R and R′, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• thio groups (HS—);
• alkylthio groups (RS—) in which the radical R is chosen from C1-C4 alkyl radicals;
• alkylsulphinyl groups (R—SO—) in which R is chosen from C1-C4 alkyl radicals;
• alkylsulphonyl groups (R—SO2—) in which R is chosen from C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• and
• halogen atoms;
• m′ is an integer ranging from 0 to 4;
• when m′ is greater than or equal to 2, two adjacent radicals R3 may form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic, containing 6 ring members, which is optionally substituted by at least one identical or different group chosen from:
• hydroxyl groups, C1-C4 alkyl groups, C1-C4 alkoxy groups, C2-C4 (poly)hydroxyalkoxy groups, C1-C4 alkylcarbonylamino groups, amino groups, amino groups substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group,
• when m′ is less than 4, then the unsubstituted carbon atom(s) of the aromatic ring carry a hydrogen atom;
• W1 radicals, which are identical, are chosen from:
• hydrogen atoms,
• halogen atoms chosen from bromine, chlorine and fluorine, and
• —NR5R6, OR7, —NR4—Ph—NR5R6, —NR4—Ph—OR7, —O—Ph—OR7 and —O—Ph—NR5R6 groups,
• wherein:
• R4 and R7, which may be identical or different, are chosen from hydrogen atoms, optionally substituted C1-C20 alkyl radicals, optionally substituted C1-C3 aralkyl radicals, and optionally substituted phenyl radicals;
• R5 and R6, which may be identical or different, are chosen from hydrogen atoms, optionally substituted C1-C20 alkyl radicals, optionally substituted phenyl radicals, optionally substituted C1-C3 aralkyl radicals, and alkylcarbonyl radicals (R—CO—) in which R is chosen from C1-C4 alkyl radicals;
• and
• R5 and R6 may optionally form, with the nitrogen atom to which they are attached, a heterocycle comprising 1 to 3 heteroatoms, chosen from N, O and S, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
• or
• R5 and R6 may optionally form, with the carbon atom of the aromatic ring adjacent to that to which —NR5R6 is attached, a 5- or 6-membered saturated heterocycle;
• Ph is chosen from optionally substituted phenyl radicals;
• L is a cationic or non-cationic linker;
• wherein the electroneutrality of the compound of formula (I) is ensured by at least one cosmetically acceptable anion (An);
• and
• a second compartment containing a composition comprising at least one oxidizing agent.